The objective of this study was to determine the prevalence of depressive symptoms in Jamaican adolescents and examine its association with individual and family factors. We used an abbreviated form of the Beck-s Depression Inventory II BDI-II to assess depressive symptoms among 748 students, attending public high schools in the parish of Hanover Jamaica. In the analysis, we classified adolescents with scores in the upper quartile of the depressive symptom score as having depressive symptoms. Multivariate logistic regression was used to determine the predictors of depressive symptoms. 14.2% of participants reported depressive symptoms. There was association between engagement in sexual activity Odds Ratio OR = 1.61, 95% Confidence Interval CI = 1.02-2.51, parental monitoring of adolescent activity OR=2.04, 95%CI=1.33 -3.12, maternal affection and support OR= 4.07, 95%CI= 2.62-6.33, and paternal affection and support OR= 1.58, 95%CI= 1.05-2.39 with self reported depressive symptoms at the bivariate level. In the final model, depressive symptoms was associated with perceived lack of maternal affection and support OR= 4.06, 95%CI= 2.61-6.32 and showed marginal association with being sexually experienced OR= 1.59, 95%CI= 1.00-2.52. As most homes are female-headed, establishing support systems for the mother to take care of their adolescent children may decrease the odds of depressive symptoms. Sexually experienced adolescents may require screening for depression. Further research is required to fully explore all factors that could predispose Jamaican adolescents to depression.